I don't think the Apple Watch is a terrible product, like many haters on here seem to. But I feel very similarly to when the iPad was announced. Shiny, new product. not quite what I was expecting, little bit let down, but little bit excited, not really sure how much I would use it in my day-to-day, seems like a luxury item just for the purpose of having more tech... One of those things that is cool just to try/have, but can't really rationalize the usefulness of buying one.
Needless to say, I waited on jumped on the iPad 2. That allowed a) thinner, more powerful product b) more easiliy identifiable use-cases c) the app ecosystem to build out d) the OS to be more refined.
I really can't imagine myself buying the Apple Watch right now. I don't really see the use-case being that great, especially for the price. It's kind of the answer to a question I didn't ask. Now when the product becomes, lighter, thinner, more powerful, better batter life, truley wireless charging, waterproof for swimming, more refined OS, built out 3rd party app ecosystem,
pay available at majority of places I shop, built in GPS (so I don't need my iPhone for runs), more friends have it so I can actually use those communicator features (although honestly, I don't think I'll ever use them... I hope that button funtionality will be customizable)... Then it will be a much more useful product.
So to answer your question, I'll probably be getting the 2nd or 3rd gen...
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I wouldn't hold your breath on the cheaper part. It is extremely rare that Apple lowers the price from 1st gen to the next. iPhone actually stayed the same price (carriers just subsidized). iPad has remained at $499 since 2010. iPad mini actually increased from $329 to $399. I'm not sure about the iPod (wasn't tracking Apple back then). The MBP and MBA have decreased in price a bit recently, but their prices (and all Mac prices) have been pretty stable for the past 10+ years.
Better, yes. Cheaper? .... doubtful. Apple may rearrange pricing structure a bit, because there are so many lines/prodcuts... but usually Apple is pretty good about picking the right number for them and sticking to it.